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Questions to ask Your Boss in a One-on-One

Hub is home to a range of talented members who are skilled in a number of different areas.

Keith Tatley, founder of the Manager Foundation, knows everything there is to know about being a great boss, and how to get the most out of employee-employer interactions.

The boss and employee one-on-one meeting is your most direct communication platform, and it’s important to go in prepared

If you’re wondering what to say in one-on-one meetings, we’re here to show you the best questions to ask your boss.
Read more: How to Attract Amazing Staff to Your Small Business

The one-on-one meeting is where you can be direct and find out what you need to know – don’t leave it up to your boss to tell you, because they’re likely to be busy, distracted, shy or unsure of what they should communicate to you.

Most employees think the boss is responsible for navigating the one-on-one meetings with employees, but as with any meeting, both people need to be involved – if you take a passive role and rely on your boss to do everything, you’re not going to get your needs met.

If you take an active role in the meeting then you can use it to get what you want from your job.

This is what you can learn to do in this free online course: 121s with your Boss. The course includes best practice one-on-one templates, plus ‘managing your boss’ tips.

These are some good questions to ask during meetings. You don’t have to (and shouldn’t) ask the entire list every time – instead, pick questions according to what you need to know and what seems to work best with your boss:

Checking in with expectations:

  • What am I doing that is working and why? Do you want more of this and how?
  • What am I doing that needs to change? Why and how?
  • What am I doing that I should stop?

Growth: Personal development, career progression:

  • What future roles do you see as suitable for my skill-set and career progression?
  • What skills should I develop to do my job better?
  • What skills should I develop to support my career progression?
  • What responsibilities can I take over as part of career development or building my network/experience?
  • Can you please give me X responsibility (because I think I can do a good job at it or it will develop my experience/network)? Many bosses prefer their employees to be proactive. If you want responsibilities, ask for them)
Read more: Why You Need to Suck Less at Explaining What You Do

Aligning priorities:

  • What is the highest priority for you?
  • What are lower priority items and what’s the possibility of these being cancelled/postponed indefinitely?
  • Is there anything I need to know about you, the team or the business?


  • Do you need resources like extra time, assistance, tools, training?
You won’t get things unless you ask, but remember to justify it and make it worthwhile.

Being helpful/being awesome:

  • What can I help with?
  • What are you struggling with?
  • What are you trying to achieve?
  • How can I support you with your own boss?

Next steps:

Self-leadership is about taking control of your life in order to achieve what you want, regardless of whether you have a good boss or not – and managing your boss starts with knowing what to say in one-on-one meetings.

Hub Australia is home to a diverse community of growing businesses based around Australia.

With locations in Brisbane, Adelaide, Sydney, and Melbourne, and more businesses joining every day, Hub Australia has the network you need to help your business grow.

Book your tour today.

About the Author - Keith Tatley

Keith Tatley is part of The Manager Foundation.